Inter-oxa-13,14-dihydro-9-deoxy-PGF compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins.

The present application is a divisional application of Ser. No. 614,243,filed Sept. 17, 1975, now issued as U.S. Pat. No. 4,033,989 on July 5,1977.

The present invention relates to prostaglandin analogs for which theessential material constituting a disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,033,989, issued July 5, 1977.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein m isone to 5, inclusive; WHEREIN M₁ is ##STR3## or ##STR4## wherein R₅ andR₆ are hydrogen or methyl, with the proviso that one of R₅ and R₆ ismethyl only when the other is hydrogen;Wherein L₁ is ##STR5## or amixture of ##STR6## and ##STR7## wherein R₃ and R₄ are hydrogen, methyl,or fluoro, being the same or different, with the proviso that one of R₃and R₄ is fluoro only when the other is hydrogen or fluoro; Wherein R₁is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms,inclusive, phenyl, phenyl substituted with one, two, or three chloro oralkyl of one to 3 carbon atoms, inclusive, or a pharmacologicallyacceptable cation; and Wherein Z₈ is (1) --CH₂ --O--CH₂ --(CH₂)_(g)--CH₂ --, (2) --(ch₂)₂ --o--(ch₂)_(g) --CH₂ --, or (3) --(CH₂)₃--O--(CH₂)_(g) --,Wherein g is one, 2, or
 3. 2. A compound according toclaim 1, wherein M₁ is ##STR8##
 3. A compound according to claim 1,wherein M₁ is ##STR9##
 4. A compound according to claim 3, wherein m is3.
 5. A compound according to claim 4, wherein Z₈ is

        --CH.sub.2 --O--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --.            


6. A compound according to claim 5, wherein g is
 3. 7. A compoundaccording to claim 5, wherein g is one.
 8. A compound according to claim7, wherein R₅ and R₆ are both hydrogen.
 9. A compound according to claim8, wherein R₃ and R₄ are both hydrogen. 10.5-Oxa-13,14-dihydro-9-deoxy-PGF₁, a compound according to claim
 9. 11. Acompound according to claim 8, wherein R₃ and R₄ are both fluoro. 12.16,16-Difluoro-5-oxa-13,14-dihydro-9-deoxy-PGF₁, a compound according toclaim
 8. 13. A compound according to claim 5, wherein Z₈ is

        --(CH.sub.2).sub.3 --O--(CH.sub.2).sub.g --.                          


14. A compound according to claim 13, wherein g is
 3. 15. A compoundaccording to claim 14, wherein R₅ and R₆ are both hydrogen.
 16. Acompound according to claim 15, wherein R₃ and R₄ are both hydrogen. 17.2a,2b-Dihomo-3-oxa-13,14-dihydro-9-deoxy-PGF₁, a compound according toclaim
 16. 18. A compound according to claim 15, wherein R₃ and R₄ areboth fluoro. 19.2a,2b-Dihomo-16,16-difluoro-3-oxa-13,14-dihydro-9-deoxy-PGF₁, a compoundaccording to claim
 18. 20. A compound according to claim 13, wherein gis one.
 21. A compound according to claim 20, wherein R₅ and R₆ are bothhydrogen.
 22. A compound according to claim 21, wherein R₃ and R₄ areboth hydrogen.
 23. 3-Oxa-13,14-dihydro-9-deoxy-PGF₁, a compoundaccording to claim
 22. 24. A compound according to claim 21, wherein R₃and R₄ are both fluoro. 25.16,16-Difluoro-3-oxa-13,14-dihydro-9-deoxy-PGF₁, a compound according toclaim 24.